Crystal Structure and DFT Study of (E)-2-chloro-4-{[2-(2,4-Dinitrophenyl)hydrazin-1-ylidene]methyl}phenol Acetonitrile Hemisolvate

Abstract

The title Schiff base compound, C<inf>13</inf>H<inf>9</inf>ClN<inf>4</inf> O<inf>5</inf>·0.5CH 3 CN, crystallizes as an acetonitrile hemisolvate; the solvent molecule being located on a twofold rotation axis. The molecule is nearly planar, with a dihedral angle between the two benzene rings oF<inf>3</inf>.7 (2)°. The configuration about the C=N bond is E, and there is an intramolecular N - H...O nitro hydrogen bond present forming an S(6) ring motif. In the crystal, molecules are linked by O - H...O and N - H...O hydrogen bonds, forming layers lying parallel to (10). The layers are linked by C - H...Cl hydrogen bonds, forming a supramolecular framework. Within the framework there are offset π-π stacking interactions [intercentroid distance = 3.833 (2) Å] present involving inversion-related molecules. The DFT study shows that the HOMO and LUMO are localized in the plane extending from the phenol ring to the 2,4-dinitrobenzene ring, and the HOMO-LUMO gap is found to be 0.13061 a.u. © 2019 Dege et al.